This dissertation argues that, during the last three decades of the nineteenth-century, at a time when, influenced by Mikhail Bakunin's philosophies of destruction, Russian revolutionaries called for the annihilation of tsarist Russia, realist novelists turned to the grotesque mode. Whereas works written by Ivan Turgenev, Sergei Aksakov, Ivan Goncharov, and Tolstoy in the 1850s and 1860s had portrayed Russia in positive terms through the lens of an idyllic countryside, three late realist novels, Fyodor Dostoevsky's Demons (1872), Mikhail Saltykov-Shchedrin's The Golovlevs (1875-1881), and Lev Tolstoy's Resurrection (1899), used the grotesque to cast a negative look at that same world. I base my definition of the grotesque on studies by Mikhail Bakhtin (Rabelais and His World) and Wolfgang Kayser (The Grotesque in Art and Literature), which describe the grotesque as an estrangement of the familiar. Kayser argues that the grotesque distorts the world as we know it; Bakhtin supplements this definition by suggesting that grotesque estrangement leads to a degradation of the abstract and spiritual to the level of physicality and the body. Working with these definitions I argue that Dostoevsky, Saltykov-Shchedrin, and Tolstoy used devices associated with earlier realism to develop their aesthetic of the grotesque and to depict Russian reality in a grotesque mode. They did not simply revive the earlier Gogolian grotesque, but created a new grotesque that estranged traditional idealizing modes of depicting life on the Russian country estate. In these late realist novels Russian reality is populated by despiritualized, grotesque beings. I set the stage for this project through an analysis of the conceptualist Vladimir Sorokin's Roman (1994), in which he simulates the pastoral idyll of the Russian countryside and then deforms and destroys it through grotesque violence. Like the nineteenth-century novelists, Sorokin reacts against the nostalgic impulse that has prevailed in Russian attitudes toward the past.